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温度

0 °C

A suspension of 12.4 g of methoxymethyl-triphenylphosphonium chloride in 120 ml of t-butyl methyl ether was treated within 3 minutes with 4.1 g of potassium t-butylate while gassing with argon at 0° C. and the mixture was stirred for a further 1 hour at 0° C. Thereafter, the mixture was treated within 10 minutes with a solution of 5.0 g of 4'-cyano-4-biphenylcarboxaldehyde in 40 ml of tetrahydrofuran and the resulting mixture was stirred for a further 1.5 hours at room temperature. The reaction mixture was subsequently poured into 200 ml of water and extracted three times with 150 ml of diethyl ether each time. The organic phases were washed twice with 150 ml of water each time, dried over magnesium sulphate and concentrated. The residue obtained was dissolved in 25 ml of ethyl acetate and the solution was treated with 350 ml of petroleum ether. After leaving to stand for 10 minutes at -20° C. the precipitated triphenylphosphine oxide was filtered off and the filtrate was concentrated to dryness. Low-pressure chromatography (0.5 bar) of the dark brown oil (9.5 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90) gave 5.2 g (91%) of 4'-(2-methoxyvinyl)-4-biphenylcarbonitrile as yellowish crystals; Rf-value (ethyl acetate/petroleum ether vol. 10:90) 0.17.

1. customwhile gassing with argon at 0° C.
2. stirringthe resulting mixture was stirred for a further 1.5 hours at room temperature
3. extractionextracted three times with 150 ml of diethyl ether each time
4. washThe organic phases were washed twice with 150 ml of water each time
5. dry with materialdried over magnesium sulphate
6. concentrationconcentrated
7. customThe residue obtained
8. customAfter leaving
9. waitto stand for 10 minutes at -20° C.
10. filtrationthe precipitated triphenylphosphine oxide was filtered off
11. concentrationthe filtrate was concentrated to dryness